Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines

Jonathan Clayden*, Lai Wah Lai, Madeleine Helliwell

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

48 Citations (Scopus)

Abstract

Condensation of atropisomeric tertiary 2-formyl naphthamides or 2-formyl benzamides with some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched form. Evidence that the reactions are under thermodynamic control is presented.

Original languageEnglish
Pages (from-to)4399-4412
Number of pages14
JournalTetrahedron
Volume60
Issue number20
Early online date26 Feb 2004
DOIs
Publication statusPublished - 10 May 2004

Keywords

  • Atropisomeric amides
  • Ephedrine
  • Imidazolines
  • Oxazolidines

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